Four optically active {(2,3,9,10,16,17,23,24-octa[(S)-2-methylbutoxy]} phthalocyanine derivatives with different central metal ions, namely (S)-H(2)Pc(β-OC(5)H(11))(8) (), (S)-ZnPc(β-OC(5)H(11))(8) (), (S)-CuPc(β-OC(5)H(11))(8) (), and (S)-NiPc(β-OC(5)H(11))(8) () have been synthesized and their self-assembly behaviors systematically investigated by electronic absorption and circular dichroism (CD) spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), X-ray diffraction (XRD) techniques, and X-ray photoelectron spectroscopy (XPS). Metal free phthalocyanine together with its zinc and copper congeners self-assembles into right-handed helical arrangements in a stack of phthalocyanine chromophores according to the CD spectroscopic result, while the nickel complex does so into the left-handed helical arrangements. These helical arrangements, acting as elemental primary structures, further pack in a hierarchical fashion into either highly ordered right-handed fibrous nanostructures with average 300 μm length, 4.8 μm width, and 4.4 μm helical pitch for and 300 μm length, 2.4 μm width, and 1.8 μm helical pitch for but left-handed fibrous nanostructures with average 4 μm length, 0.48 μm width, and 0.12 μm helical pitch for and 300 μm length, 2 μm width, and 1.2 μm helical pitch for , clearly revealing the effect of central metal ion on the distance and relative orientation of neighboring phthalocyanine chromophores and in turn the supramolecular chirality, morphology, dimension, and handedness of the self-assembled nanostructures. The present result not only represents a unique phenomenon in the self-assembly of phthalocyanine compounds but more importantly denotes the transcription and amplification of molecular chirality to supramolecular helicity with different helical bias during the self-assembly processes without changing the chiral handles attached to the phthalocyanine chromophore.